CN114014771A - Ultrahigh-purity amino acid, and preparation method and application thereof - Google Patents
Ultrahigh-purity amino acid, and preparation method and application thereof Download PDFInfo
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- CN114014771A CN114014771A CN202110734028.8A CN202110734028A CN114014771A CN 114014771 A CN114014771 A CN 114014771A CN 202110734028 A CN202110734028 A CN 202110734028A CN 114014771 A CN114014771 A CN 114014771A
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- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
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- 239000004472 Lysine Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Water Treatment By Electricity Or Magnetism (AREA)
Abstract
The invention relates to a method for purifying ultrahigh-purity amino acid, which comprises the following steps: taking amino acid with the purity of more than 99%, stirring and dissolving the amino acid in deionized water to obtain an amino acid solution to be purified, and sequentially carrying out activated carbon decoloration, electrodialysis impurity removal and ion exchange resin filtration to obtain the high-purity amino acid with the purity of more than 99.99%. The invention can improve the purity of amino acid from 99% to 99.99%, and reduce the content of single metal ion in the product to below 20ppb, thus meeting the requirement of amino acid for electronic chemicals.
Description
Technical Field
The invention relates to the technical field of biological preparation, in particular to an ultra-high-purity amino acid, a preparation method and application thereof.
Background
The electronic chemicals, also called ultra-clean high-purity reagents, can be used in the etching, cleaning, developing and electroplating processes of wafers, chips and PCB boards in the field of manufacturing microelectronic devices such as semiconductors, flat panel displays, solar cells and the like. The purity of the electronic chemicals is high, and the number of impurity ions and particles is required to meet the requirements of international standard grade SEMI for electronic chemicals so as to avoid the damage of the impurity ions to the circuit function between chips in the integrated circuit.
Research has shown that ultra-high purity amino acids (greater than 99.99% purity) can be used as electronic chemicals. However, amino acids can carry many impurity ions (such as Na) in the production process+、Mg2+、Al3+、K+Etc.), cannot be removed by conventional purification methods, so that its large-scale application in the field of electronics industry is limited. Therefore, there is a need in the art to develop ultra-high purity amino acids having low impurity ion content.
Disclosure of Invention
The invention aims to provide a method for preparing ultrahigh-purity amino acid, which comprises the following steps: taking amino acid with the purity of more than 99%, stirring and dissolving the amino acid in deionized water to obtain an amino acid solution to be purified, and sequentially carrying out activated carbon decoloration, electrodialysis impurity removal and ion exchange resin filtration to obtain the high-purity amino acid with the purity of more than 99.99%.
According to the preferable technical scheme of the invention, the concentration of the amino acid in the amino acid solution to be purified is 60-200g/L, and preferably 80-100 g/L.
According to the preferable technical scheme, the step of decolorizing with activated carbon is to add 0.5-1.0 vt% of activated carbon into the amino acid solution to be purified, stir and decolorize for 0.5-1.0h at 50-60 ℃ to obtain the decolorized clear liquid of activated carbon.
According to the preferable technical scheme, the light transmittance of the activated carbon decoloration clear liquid is more than or equal to 90%, and the preferable light transmittance is more than or equal to 99%.
According to the preferable technical scheme, the activated carbon is washed by deionized water, the conductivity of the washed solution is not higher than 1.0 mu s/cm, and the activated carbon can be repeatedly used.
According to the preferable technical scheme, the electrodialysis step is that an electrodialysis device with the voltage of 10-50V and the current of 50-200 Ma is fed into the decolorized clear liquid of the activated carbon to remove impurities for 0.5-1h, and the electrodialysis impurity-removed clear liquid is obtained.
According to the preferable technical scheme, the ion exchange resin comprises the steps of sequentially feeding electrodialysis impurity-removed clear liquid into cation resin and anion resin at the flow rate of 1-10 column volumes/h, and reacting for 0.5-1 hour to obtain resin effluent liquid.
According to the preferable technical scheme of the invention, the working temperature of the resin is 20-60 ℃, and preferably 35-45 ℃.
In a preferred embodiment of the present invention, the height/diameter ratio of the resin is (3-10):1, preferably (5-8): 1.
According to the preferable technical scheme, the flow rate of the electrodialysis impurity removal clear solution is 2-6 column volumes/h, and is preferably 3-4 column volumes/h.
In a preferred embodiment of the present invention, the cationic resin is any one of types D001 and 732, or a combination thereof.
In a preferred embodiment of the present invention, the type of the anionic resin is any one of D301 and D202, or a combination thereof.
According to the preferable technical scheme, the resin effluent is subjected to evaporation concentration, cooling and crystal growing, centrifugation, washing and drying treatment to obtain the ultra-high-purity alanine.
According to the preferable technical scheme, the evaporation concentration step is to concentrate the resin effluent for 2-3 hours at 50-80 ℃ under-0.5 to-1.5 Mpa until a large amount of crystals are separated out to obtain the concentrated solution.
According to the preferable technical scheme, the step of cooling and growing the crystals comprises the steps of cooling the concentrated solution to 0-25 ℃, growing the crystals for 3-5 hours at 20-50r/min, and centrifuging to obtain the crystals.
According to the preferable technical scheme, the drying is that the crystal is dried for 5-6 hours at the temperature of 80-120 ℃.
According to the preferable technical scheme of the invention, the content of single metal ions in the high-purity amino acid is 0-20 ppb, preferably 0-10ppb, and more preferably 0-5 ppb.
According to the preferable technical scheme of the invention, the single metal ion is Na+、Mg2+、Al3+、K+、Ca2+、Fe2+、Fe3+Any one of the above.
According to the preferable technical scheme, the content of amino acid in the high-purity amino acid is more than or equal to 99.99%.
In a preferred embodiment of the present invention, the amino acid is selected from any one of alanine, glycine, valine, leucine, isoleucine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, threonine, aspartic acid, glutamic acid, lysine, methionine, arginine, and histidine, preferably, the amino acid is any one of alanine, arginine, and cysteine, preferably, the alanine is selected from any one of L-alanine, DL-alanine, D-alanine, and β -alanine, and more preferably, the alanine is selected from any one of L-alanine and β -alanine.
It is another object of the present invention to provide a high purity amino acid, said amino acid having a purity of greater than 99.99%.
According to the preferable technical scheme of the invention, the content of single metal ions in the high-purity amino acid is 0-20 ppb, preferably 5-10 ppb.
According to the preferable technical scheme of the invention, the single metal ion is Na+、Mg2+、Al3+、K+、Ca2+、Fe2+、Fe3+Any one of the above.
Another object of the present invention is to provide the use of the high purity amino acids of the present invention in electronic chemicals.
According to the preferable technical scheme, the electronic chemicals are any one of a metal complexing agent, a metal etching solution, a circuit board cleaning agent, a template guiding agent, a photoresist cleaning agent, a crosslinking modifier, a polishing solution and an electrode modification material.
Unless otherwise indicated, when the present invention relates to percentages between liquids, said percentages are volume/volume percentages; the invention relates to the percentage between liquid and solid, said percentage being volume/weight percentage; the invention relates to the percentages between solid and liquid, said percentages being weight/volume percentages; the balance being weight/weight percent.
Compared with the prior art, the invention has the following beneficial technical effects:
1. the invention provides a preparation method of high-purity amino acid, which can improve the purity of the amino acid from 99% to 99.99%, and simultaneously reduce the content of single metal ions in the product to below 20ppb, thereby meeting the requirement of the amino acid for electronic chemicals.
2. The purification method of the invention is convenient to operate and is suitable for industrial production.
Detailed Description
The present invention is further illustrated in detail by the following examples. These examples and experimental examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The electrodialysis apparatus used in the examples was commercially available under the model number GCM-E-10 with 10 membrane pairs.
Example 1
(1) Adding 18.5L deionized water into 1850g of alanine with the purity of 99.0% to dissolve to prepare an L-alanine solution with the concentration of 100 g/L;
(2) adding active carbon into alanine solution according to the addition amount of 0.5-1.0 vt%, stirring and decolorizing for 0.5-1.0h under 50-60 ℃ water bath environment, filtering to obtain 17.3L of decolorized clear liquid, wherein the light transmittance of the decolorized clear liquid is 99.99%, washing the active carbon with deionized water until the conductivity is less than 1.0 mu s/cm, and continuously recycling;
(3) introducing the decolorized clear solution into a desalting chamber of an electrodialyzer, performing electrodialysis for 30 minutes under the voltage of 25V, collecting the solution in a concentration chamber, and preparing electrodialysis impurity-removed clear solution;
(4) and (3) passing the electrodialysis impurity removal clear solution through an anion resin column D301 and a cation resin column D001 in sequence, wherein the height ratio of the two resin columns is 8: 1, the internal resin filling diameter-height ratio is 6: 1, filling amount of the anion column resin and the cation column resin is 300g, flow rate is 3-4BV, working temperature of the resin is 35-45 ℃, and effluent liquid is collected for 16.8L;
(5) transferring the effluent to a 30L single-effect concentration tank, and concentrating at 65 deg.C under-0.95 Mpa for 2-3 hr at 20r/min until a large amount of crystals are separated out to obtain 6.2L of concentrated solution;
(6) cooling the concentrated solution to 10 ℃, adjusting the stirring speed to 10r/min, growing crystals for 3-5 hours, centrifuging the crystallization solution, collecting crystals, leaching the crystals with 2-3L of deionized water, collecting crystals, and drying at 105 ℃ for 5-6 hours to obtain 1100g of alanine product.
The alanine product is subjected to component content detection, and the detection result of metal ions is shown in table 1. The purity of the alanine is more than or equal to 99.99 percent.
TABLE 1
| Metal ion | Content/ppb |
| Na | 19 |
| Mg | 8 |
| Al | 2 |
| K | 11 |
| Ca | 16 |
| Fe | 3 |
Example 2
(1) Adding 18.5L deionized water into 1850g of valine with the purity of 99.0% to dissolve to prepare an L-alanine solution with the concentration of 100 g/L;
(2) adding activated carbon into a valine solution according to the addition amount of 0.5-1.0 vt%, stirring and decoloring for 0.5-1.0h under a water bath environment at 50-60 ℃, filtering to obtain 17.3L of decolored clear liquid, wherein the light transmittance of the decolored clear liquid is 99.99%, and the activated carbon is washed by deionized water until the conductivity is less than 1.0 mu s/cm and can be continuously recycled;
(3) introducing the decolorized clear solution into a desalting chamber of an electrodialyzer, performing electrodialysis for 30 minutes under the voltage of 25V, collecting the solution in a concentration chamber, and preparing electrodialysis impurity-removed clear solution;
(4) and (3) passing the electrodialysis impurity removal clear solution through an anion resin column D301 and a cation resin column D001 in sequence, wherein the height ratio of the two resin columns is 8: 1, the internal resin filling diameter-height ratio is 6: 1, filling amount of the anion column resin and the cation column resin is 300g, flow rate is 3-4BV, working temperature of the resin is 35-45 ℃, and effluent liquid is collected for 16.8L;
(5) transferring the effluent to a 30L single-effect concentration tank, and concentrating at 65 deg.C under-0.95 Mpa for 2-3 hr at 20r/min until a large amount of crystals are separated out to obtain 6.2L of concentrated solution;
(6) cooling the concentrated solution to 10 ℃, adjusting the stirring speed to 10r/min, growing crystals for 3-5 hours, centrifuging the crystallization solution, collecting crystals, leaching the crystals with 2-3L of deionized water, collecting crystals, and drying at 105 ℃ for 5-6 hours to obtain 1100g of valine product.
The component content of the valine product is detected, and the detection result of the metal ions is shown in table 2. The purity of the valine is more than or equal to 99.99 percent.
TABLE 2
| Metal ion | Content/ppb |
| Na | 17 |
| Mg | 10 |
| Al | 3 |
| K | 10 |
| Ca | 12 |
| Fe | 2 |
The above description of the specific embodiments of the present invention is not intended to limit the present invention, and those skilled in the art may make various changes and modifications according to the present invention without departing from the spirit of the present invention, which is defined in the appended claims.
Claims (10)
1. A method for producing an ultra-high purity amino acid, comprising the steps of: taking amino acid with the purity of more than 99%, stirring and dissolving the amino acid in deionized water to obtain an amino acid solution to be purified, and sequentially carrying out activated carbon decoloration, electrodialysis impurity removal and ion exchange resin filtration to obtain the high-purity amino acid with the purity of more than 99.99%.
2. The method according to claim 1, wherein the concentration of the amino acid in the solution of the amino acid to be purified is 60 to 200g/L, preferably 80 to 100 g/L.
3. The method according to any one of claims 1 to 2, wherein the activated carbon decolorization step is to add 0.5 to 1.0 vt% of activated carbon to the amino acid solution to be purified, and to decolorize the solution at 50 to 60 ℃ for 0.5 to 1.0h with stirring to obtain an activated carbon decolorized clear solution.
4. The method according to any one of claims 1 to 3, wherein the light transmittance of the decolorized clear liquid of activated carbon is 90% or more, preferably 99% or more.
5. The method according to any one of claims 1 to 4, wherein the electrodialysis step is to feed the decolorized clear liquid of the activated carbon into an electrodialysis device with the voltage of 10-50V and the current of 50-200 Ma to remove impurities for 0.5-1h to obtain the electrodialysis impurity-removed clear liquid.
6. The method according to any one of claims 1 to 5, wherein the ion exchange resin step is a step of feeding the electrodialysis clarified liquid into the cationic resin and the anionic resin in this order at a flow rate of 1 to 10 column volumes/h, and reacting for 0.5 to 1 hour to obtain a resin effluent.
7. The method according to any one of claims 1 to 6, wherein the resin effluent is subjected to evaporation concentration, temperature reduction and crystal growth, centrifugation, washing and drying to obtain the ultra-high purity alanine.
8. The method according to any one of claims 1 to 7, wherein the high-purity amino acid has a content of a single metal ion of 0 to 20ppb, preferably 0 to 10ppb, more preferably 0 to 5ppb, and the single metal ion is Na+、Mg2+、Al3+、K+、Ca2+、Fe2+、Fe3+Any one of the above.
9. The highly pure amino acid produced by the method according to any one of claims 1 to 8, wherein the purity of the amino acid is more than 99.99%, preferably the content of a single metal ion in the highly pure amino acid is 0 to 20ppb, preferably 5 to 10ppb, and preferably the single metal ion is Na+、Mg2+、Al3+、K+、Ca2+、Fe2+、Fe3+Any one of the above.
10. Use of the high purity amino acid according to claim 9 in an electronic chemical, preferably said electronic chemical is any one of a metal complexing agent, a metal etching solution, a circuit board cleaning agent, a template directing agent, a photoresist cleaning agent, a crosslinking modifier, a polishing solution, and an electrode modification material.
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Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1387458A (en) * | 1999-11-03 | 2002-12-25 | 巴斯福股份公司 | Method for purification of amino acid contg. solutions by electrodialysis |
| CN101100437A (en) * | 2007-08-15 | 2008-01-09 | 安徽天润得生物工程有限公司 | Method for preparing high-purity beta-alanine |
| CN101275057A (en) * | 2007-03-30 | 2008-10-01 | 富士胶片株式会社 | Metal-polishing liquid and polishing method |
| CN102964261A (en) * | 2012-04-17 | 2013-03-13 | 肖文辉 | Preparation method of ornithine aspartate |
| CN104419930A (en) * | 2013-08-27 | 2015-03-18 | 东友精细化工有限公司 | Ethicng liquid composition, and method for preparing array substrate for use in liquid crystal display device |
| CN104710319A (en) * | 2015-01-22 | 2015-06-17 | 重庆紫光化工股份有限公司 | Green environmentally-friendly method for combined production of amino acid and analog thereof by using membrane integration technology |
| WO2016152091A1 (en) * | 2015-03-20 | 2016-09-29 | パナソニックＩｐマネジメント株式会社 | Etching liquid for multilayer film, etching concentrate, and etching method |
| CN106544372A (en) * | 2016-11-04 | 2017-03-29 | 广西多得乐生物科技有限公司 | A kind of method that gamma aminobutyric acid is purified from zymotic fluid |
| CN107760735A (en) * | 2017-12-13 | 2018-03-06 | 湖北新生源生物工程有限公司 | A kind of method that L glutamic acid is separated from electrodialysis fresh water |
| CN108362751A (en) * | 2018-01-23 | 2018-08-03 | 武汉工程大学 | The preparation method and applications of electrochemistry alanine biosensor based on boron-doped diamond microelectrode |
| CN110003029A (en) * | 2019-04-10 | 2019-07-12 | 南通光荣化工有限公司 | A kind of electron level iminodiacetic acid method of purification |
| CN110643547A (en) * | 2019-11-07 | 2020-01-03 | 巴彦淖尔华恒生物科技有限公司 | Brevibacterium flavum for producing L-valine and method for producing L-valine by using same |
| CN111718272A (en) * | 2020-07-14 | 2020-09-29 | 安徽华恒生物科技股份有限公司 | Preparation method and application of alanine metal chelate |
| CN111718287A (en) * | 2020-06-12 | 2020-09-29 | 吉林大学 | Electrodialysis extraction method of N-acetyl-L-cysteine |
| CN112979482A (en) * | 2020-12-25 | 2021-06-18 | 安徽华恒生物科技股份有限公司 | High-purity L-valine and preparation method and application thereof |
-
2021
- 2021-06-30 CN CN202110734028.8A patent/CN114014771B/en active Active
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1387458A (en) * | 1999-11-03 | 2002-12-25 | 巴斯福股份公司 | Method for purification of amino acid contg. solutions by electrodialysis |
| CN101275057A (en) * | 2007-03-30 | 2008-10-01 | 富士胶片株式会社 | Metal-polishing liquid and polishing method |
| CN101100437A (en) * | 2007-08-15 | 2008-01-09 | 安徽天润得生物工程有限公司 | Method for preparing high-purity beta-alanine |
| CN102964261A (en) * | 2012-04-17 | 2013-03-13 | 肖文辉 | Preparation method of ornithine aspartate |
| CN104419930A (en) * | 2013-08-27 | 2015-03-18 | 东友精细化工有限公司 | Ethicng liquid composition, and method for preparing array substrate for use in liquid crystal display device |
| CN104710319A (en) * | 2015-01-22 | 2015-06-17 | 重庆紫光化工股份有限公司 | Green environmentally-friendly method for combined production of amino acid and analog thereof by using membrane integration technology |
| WO2016152091A1 (en) * | 2015-03-20 | 2016-09-29 | パナソニックＩｐマネジメント株式会社 | Etching liquid for multilayer film, etching concentrate, and etching method |
| CN106544372A (en) * | 2016-11-04 | 2017-03-29 | 广西多得乐生物科技有限公司 | A kind of method that gamma aminobutyric acid is purified from zymotic fluid |
| CN107760735A (en) * | 2017-12-13 | 2018-03-06 | 湖北新生源生物工程有限公司 | A kind of method that L glutamic acid is separated from electrodialysis fresh water |
| CN108362751A (en) * | 2018-01-23 | 2018-08-03 | 武汉工程大学 | The preparation method and applications of electrochemistry alanine biosensor based on boron-doped diamond microelectrode |
| CN110003029A (en) * | 2019-04-10 | 2019-07-12 | 南通光荣化工有限公司 | A kind of electron level iminodiacetic acid method of purification |
| CN110643547A (en) * | 2019-11-07 | 2020-01-03 | 巴彦淖尔华恒生物科技有限公司 | Brevibacterium flavum for producing L-valine and method for producing L-valine by using same |
| CN111718287A (en) * | 2020-06-12 | 2020-09-29 | 吉林大学 | Electrodialysis extraction method of N-acetyl-L-cysteine |
| CN111718272A (en) * | 2020-07-14 | 2020-09-29 | 安徽华恒生物科技股份有限公司 | Preparation method and application of alanine metal chelate |
| CN112979482A (en) * | 2020-12-25 | 2021-06-18 | 安徽华恒生物科技股份有限公司 | High-purity L-valine and preparation method and application thereof |
Non-Patent Citations (7)
| Title |
|---|
| ARMEN AGHAJANYAN, 等，: "Development of the efficient technology for isolating proline from culture liquid", SEPARATION SCIENCE AND TECHNOLOGY, pages 1 - 9 * |
| 张雪;令狐青青;童晓倩;毛贵珠;罗红宇;宋茹;: "响应面法优化鱿鱼(Ommastrephes bartrami)皮胶原蛋白提取液脱色工艺", 海洋与湖沼, no. 01, pages 221 - 227 * |
| 林冠丽;余泳瑜;邱楚钰;周剑峰;孙国瀚;翟海云;: "电聚合L-半胱氨酸修饰电极的研制及其对L-酪氨酸的分析", 化学研究与应用, no. 01, pages 28 - 33 * |
| 沈英;: "超洁净和高纯度电子级醋酸的生产方法", 乙醛醋酸化工, no. 09, pages 35 - 37 * |
| 熊能，等: "电渗析技术在氨基酸分离中的应用进展与趋势", 食品与发酵工业, vol. 45, no. 16, pages 286 - 292 * |
| 王焯筠;刘萌;: "论混合氨基酸溶液中分离制备丝氨酸的研究", 化工管理, no. 23, pages 62 - 63 * |
| 田宋魁，等: "L-丙氨酸生产工艺的研究进展", 精细与专用化学品, vol. 25, no. 08, pages 12 - 14 * |
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